The present invention relates to novel substituted 3-phenylpyrazoles of the formula I 
in which
R1 is hydrogen, cyano, nitro, halogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, cyano-C1-C4-alkyl, C1-C8alkyl-Oxe2x80x94R6, C1-C8-alkyl- Oxe2x80x94COxe2x80x94R6, C2-C8-alkenyl-Oxe2x80x94R6, C2-C8-alkynyl-Oxe2x80x94R6, C1-C8-alkyl-Sxe2x80x94R6, C2-C8-alkenyl-Sxe2x80x94R6, C2-C8-alkynyl-Sxe2x80x94R6, C1-C8-alkyl-SOxe2x80x94R6, C2-C8-alkenyl-SOxe2x80x94R6, C2-C8-alkynyl-SOxe2x80x94R6, C1-C8-alkyl-SO2xe2x80x94R6, C2-C8-alkenyl-SO2xe2x80x94R6; C2-C8-alkynyl-SO2xe2x80x94R6, xe2x80x94Oxe2x80x94R6, xe2x80x94Sxe2x80x94R6, xe2x80x94SOxe2x80x94R6, xe2x80x94SO2xe2x80x94R6, xe2x80x94SO2xe2x80x94Cl, xe2x80x94SO2xe2x80x94Oxe2x80x94R6, xe2x80x94SO2xe2x80x94N(R7,R8), xe2x80x94SO2xe2x80x94N(R7)xe2x80x94COxe2x80x94R9, xe2x80x94N(R7R8), xe2x80x94N(R7) xe2x80x94N(R8,R32), xe2x80x94Nxe2x95x90Nxe2x80x94COxe2x80x94R9, xe2x80x94N(R7)xe2x80x94N(R8)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94SO2xe2x80x94R11, xe2x80x94N(SO2xe2x80x94R11)(SO2xe2x80x94R12), xe2x80x94N(SO2xe2x80x94R11)(COxe2x80x94R9), xe2x80x94NHxe2x80x94COxe2x80x94Oxe2x80x94R6, xe2x80x94Oxe2x80x94COxe2x80x94NHxe2x80x94R7, xe2x80x94Oxe2x80x94COxe2x80x94R9, xe2x80x94NHxe2x80x94COxe2x80x94NHxe2x80x94R13, xe2x80x94Oxe2x80x94CSxe2x80x94N(C1-C4-alkyl)2, xe2x80x94Oxe2x80x94CSxe2x80x94NH2, xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94R6, xe2x80x94Axe2x80x94P(O)(OR6)2, xe2x80x94Oxe2x80x94(C1-C4-alkyl)-COOR6, xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94Nxe2x95x90C(R14,R15), xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94CH2xe2x80x94Oxe2x80x94Nxe2x95x90C(R16,R17), xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94C(R18,R19)xe2x80x94CH2xe2x80x94Oxe2x80x94Nxe2x95x90C(R16,R17), xe2x80x94Axe2x80x94COxe2x80x94N(R7,R8), xe2x80x94Axe2x80x94CSxe2x80x94N(R7,R8), xe2x80x94Axe2x80x94COxe2x80x94NHxe2x80x94SO2xe2x80x94(C1-C4-alkyl), xe2x80x94Axe2x80x94COxe2x80x94R20, xe2x80x94Axe2x80x94CHxe2x95x90Nxe2x80x94Oxe2x80x94R6, xe2x80x94Axe2x80x94CH(XR21, YR22), xe2x80x94Axe2x80x94C(R20)xe2x95x90Nxe2x80x94Oxe2x80x94R6, xe2x80x94(C1-C4-alkyl)-Oxe2x80x94(C1-C4-alkyl)xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl), isoxazolidinylcarbonyl, xe2x80x94Axe2x80x94COxe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COxe2x80x94N(R32,R33), 
R2 is cyano, trifluoromethyl or halogen;
R3 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl;
R4 is C1-C4-alkyl or C1-C4-haloalkyl;
R5 is hydrogen, nitro, halogen, xe2x80x94COOR29 or xe2x80x94COxe2x80x94N(R30,R31);
Z is oxygen, sulfur, xe2x80x94SOxe2x80x94 or xe2x80x94SO2xe2x80x94;
X and Y independently of one another are oxygen or sulfur;
A is a chemical bond, methylene, ethylene, 1,3-propylene, 1,4-butylene, vinylene or 1,4-butadienylene;
R6,R29 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C3-C7-cycloalkyl which may in turn carry from one to three C1-C3-alkyl radicals, C3-C6-alkenyl, C5-C7-cycloalkenyl which may in turn carry from one to three C1-C3-alkyl radicals, C3-C6-haloalkenyl, cyano-C1-C8-alkyl, C3-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, 2-tetrahydrofuryl-C1-C8-alkyl, 3-oxetanyl, 3-thietanyl, carboxyl-C1-C6-alkyl, (C1-C8-alkoxy)carbonyl-C1-C6-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy)carbonyl-C1-C6-alkyl, cyclopropylmethyl, (1-methylthiocycloprop-1-yl)methyl, C3-C9-(xcex1-alkylalkylidene)-iminooxy-C1-C6-alkyl, (C1-C4-alkyl)carbonyl, C1-C4-alkyl which is substituted by xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-haloalkyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C3-C6-alkenyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C3-C6-haloalkenyl) or xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl)-R34, phenyl, phenyl-C1-C6-alkyl, phenyl-C2-C6-alkenyl, phenyl-C3-C6-alkynyl or phenoxy-C1-C6-alkyl, the phenyl ring being able in each case to be unsubstituted or in turn to carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl and C2-C6-alkenyl, 5- or 6-membered heteroaryl, heteroaryl-C1-C6-alkyl, heteroaryl-C3-C6-alkenyl, heteroaryl-C3-C6-alkynyl or heteroaryloxy-C1-C6-alkyl, the heteroaromatic radical containing in each case from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able, if desired, to carry on each substitutable ring member a radical selected in each case from the group consisting of hydroxyl, halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-alkyl;
R7,R8,R13,R30,R31,R32,R33 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, cyano-C1-C8-alkyl, carboxyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, (C3-C6-cycloalkoxy)carbonyl-C1-C4-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy)carbonyl-C1-C4-alkyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, tetrahydrofuran-2-on-3-yl, phenyl, phenyl-C1-C4-alkyl, in which the phenyl ring may in each case be unsubstituted or may carry one to three radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl and C2-C6-alkenyl, 5- or 6-membered heteroaryl or heteroaryl-C1-C4-alkyl, the heteroaromatic radical containing from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able, if desired, to carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-haloalkyl; or
R7 and R8 and/or R30 and R31 are together a tetramethylene, pentamethylene or ethyleneoxyethylene chain which may if desired carry from one to three C1-C4-alkyl radicals and/or a radical xe2x80x94COOR6;
R9 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C7-cycloalkyl which may in turn carry from one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-alkylthio, phenyl or phenyl-C1-C6-alkyl, in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-haloalkyl;
R10 is hydrogen, C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl or the equivalent of an agriculturally usable cation;
R11 and R12 independently of one another are C1-C4-alkyl, C1-C4-haloalkyl, phenyl which may be unsubstituted or may carry from one to three substituents in each case selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-haloalkyl, or 5- or 6-membered heteroaryl containing from one to three heteroatoms selected from the group consisting of 2 nitrogen atoms and one oxygen or sulfur atom, the heteroaromatic radical being able to be unsubstituted or to carry, if desired, on each substitutable ring member a substituent in each case selected from the group consisting of hydroxyl, halogen C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkylthio;
R14 is C1-C6-alkyl, C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl or (C1-C6-alkoxy)carbonyl-C1-C4-alkyl;
R15 is C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy-C1-C4-alkyl, (C1-C6-alkoxy)carbonyl-C1-C4-alkyl, di-[(C1-C6-alkoxy)carbonyl]-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkoxy)carbonyl, 2-furyl or phenyl, both of which may be unsubstituted or, if desired, may carry from one to three radicals selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy; consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy; or
R14 and R15 together with the carbon atom to which they are attached, are a cyclopentane or cyclohexane ring which may if desired in turn carry from one to three C1-C4-alkyl radicals;
R16 is hydrogen or C1-C6-alkyl;
R17 is C1-C6-alkyl, C3-C6-cycloalkyl or phenyl;
R18 is hydrogen or C1-C4-alkyl;
R19 is hydrogen, C1-C4-alkyl, phenyl or benzyl;
R20 is hydrogen, cyano, halogen, C1-C4-alkyl, C1-C4-alkylthio, C2-C4-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, di-(C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, (1,3-dioxolan-2-yl)-C1-C4-alkyl or (1,3-dioxan-2-yl)-C1-C4-alkyl;
R21 and R22 independently of one another are C1-C8-alkyl, C1-C8-haloalkyl or C1-C4-alkoxy-C1-C4-alkyl;
R23,R24,R25,R26,R27 and R28 independently of one another are hydrogen, cyano, C1-C8-alkyl, C1-C8-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy, xe2x80x94COxe2x80x94Oxe2x80x94R6, xe2x80x94COxe2x80x94N(R7,R8), xe2x80x94COxe2x80x94R20, xe2x80x94Sxe2x80x94R6, xe2x80x94SO2xe2x80x94R6, xe2x80x94Oxe2x80x94COxe2x80x94R9 or C3-C7-cycloalkyl which may in turn carry from one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-alkylthio;
R34 is phenyl or 5- or 6-membered heteroaryl containing from one to three heteroatoms selected from the group consisting of 2 nitrogen atoms and one oxygen or sulfur atom, each phenyl or heteroaryl ring being able to be unsubstituted or, if desired, to carry on each substitutable ring member a substituent in each case selected from the group consisting of hydroxyl, nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-alkylthio,
and to the agriculturally usable salts of I.
The invention also relates to the use of these compounds as herbicides, to herbicidal compositions which comprise the compounds I as active substances, to methods of producing these herbicidal compositions and to methods of controlling unwanted plant growth using the compounds I.
JP 03/151 367 describes herbicidally active 1-(1-alkyl-4-halo-5-haloalkoxy-1H-pyrazol-3-yl)-4,6-dihalophenyl derivatives having the various substituents in position 3 of the phenyl ring, especially compounds having the following pattern of substitution IIa; 
Furthermore, EP-A 443 059 teaches that 1-alkyl- and 1-haloalkyl-3-(4-chloro-6-halophenyl)-pyrazoles and -4-halopyrazoles which carry particular substituents in position 3 of the phenyl ring and which are substituted in position 5 of the pyrazole ring by hydroxyl, mercapto, lower alkoxy, alkylthio, haloalkoxy or haloalkylthio are suitable for controlling unwanted plants.
Furthermore, JP-A 03/072 460 discloses that 3-substituted phenylpyrazoles of the formula IIb 
in which Ra is hydrogen, halogen or cyano and Rb is lower alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl are herbicidally active.
EP-A 447 055 discloses that 1-(lower alkyl)-3-(4-chloro-6-halophenyl)-4-halo-5-difluoromethoxypyrazoles which carry an alkylthiocarbonyl, alkenylthiocarbonyl or benzylthiocarbonylmethoxycarbonyl group in position 3 of the phenyl ring exhibit herbicidal activity.
In accordance of the teaching of JP-A 03/047 180 and JP-A 03/081 275 pyrazole derivatives, inter alia, of the formulae IIc and IId 
in which
Rc is hydrogen, methyl or allyl and
Rd is hydrogen, ethyl, allyl or propargyl
are suitable as herbicides.
According to JP-A 02/300 173 and JP-A 03/093 774, specific 1-alkyl-3-phenylpyrazoles which may carry from one to four halogen atoms on the phenyl ring likewise exhibit herbicidal activity. Particular mention is made of 1-methyl-3-(2,4-dichlorophenyl)pyrazoles and three 1-methyl-5-chloro-3-(2-fluoro-4-chlorophenyl)pyrazoles.
Finally, WO 92/06962 describes herbicidal 4-halo-5-haloalkyl-3-phenylpyrazoles having various substituents on the phenyl ring.
The herbicidal properties of the known herbicides with respect to weed plants, however, are able to give only limited satisfaction.
It is an object of the present invention therefore to provide novel herbicidally active compounds which can be used to give better, targeted control of unwanted plants than hitherto.
We have found that this object is achieved by the substituted 3-phenylpyrazoles of the formula I. We have also found herbicidal compositions which comprise the compounds I and possess a very good herbicidal activity. Moreover, we have found methods of producing these compositions and methods of controlling unwanted plant growth using the compounds I.
With regard to the use of the substituted 3-phenylpyrazoles I as herbicides, preferred compounds I are those in which, in each case individually or in combination:
R1 is hydrogen, nitro, halogen, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkyl-Oxe2x80x94R6, C1-C8-alkyl-Oxe2x80x94COxe2x80x94R6, C1-C8-alkyl-Sxe2x80x94R6, C1-C8-alkyl-SOxe2x80x94R6, C1-C8-alkyl-SO2xe2x80x94R6, xe2x80x94Oxe2x80x94R6, xe2x80x94SO2xe2x80x94R6, xe2x80x94SO2xe2x80x94Oxe2x80x94R6, xe2x80x94SO2xe2x80x94N(R7,R8), xe2x80x94N(R7,R8), xe2x80x94N(R7)xe2x80x94N(R8,R32)xe2x80x94Nxe2x95x90Nxe2x80x94COxe2x80x94R9, xe2x80x94N(R7)xe2x80x94N(R8)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94SO2xe2x80x94R11, xe2x80x94N(SO2xe2x80x94R11)(SO2xe2x80x94R12), xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94R6, xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94C(R18,R19)xe2x80x94CH2xe2x80x94Oxe2x80x94Nxe2x95x90C(R16,R17), xe2x80x94Axe2x80x94COxe2x80x94N(R7,R8), xe2x80x94Axe2x80x94COxe2x80x94R20, xe2x80x94Axe2x80x94CH(XR21, YR22), xe2x80x94(C1-C4-alkyl)xe2x80x94Oxe2x80x94(C1-C4-alkyl)xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl), xe2x80x94Axe2x80x94COxe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COxe2x80x94N(R32,R33) 
xe2x80x83particular preference is given to hydrogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkyl-Oxe2x80x94R6, C1-C8-Alkyl-Oxe2x80x94COxe2x80x94R6, C1-C8-alkyl-Sxe2x80x94R6, C1-C8-alkyl-SOxe2x80x94R6, xe2x80x94SO2xe2x80x94R6, xe2x80x94SO2xe2x80x94Oxe2x80x94R6, xe2x80x94SO2xe2x80x94N(R7,R8), xe2x80x94N(R7,R8), xe2x80x94N(R7)xe2x80x94N (R8,R32), xe2x80x94Nxe2x95x90Nxe2x80x94COxe2x80x94R9, xe2x80x94N(R7)xe2x80x94N (R8)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94COxe2x80x94R9, xe2x80x94N(R10)xe2x80x94SO2xe2x80x94R11, xe2x80x94N(SO2xe2x80x94R11)(SO2xe2x80x94R12), xe2x80x94Axe2x80x94COxe2x80x94Oxe2x80x94R6, xe2x80x94Axe2x80x94COxe2x80x94N(R7, R8), xe2x80x94Axe2x80x94COxe2x80x94R20, xe2x80x94Axe2x80x94CH(XR21, YR22), xe2x80x94Axe2x80x94COxe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COOR6, xe2x80x94SO2xe2x80x94N(R7)xe2x80x94C(R8,R18)xe2x80x94COxe2x80x94N(R32,R33), 
R2 is cyano, trifluoromethyl or halogen;
R3 is C1-C4-alkyl or C1-C4-haloalkyl;
R4 is C1-C4-alkyl or C1-C4-haloalkyl;
R5 is nitro, halogen, xe2x80x94COOR29 or xe2x80x94COxe2x80x94N(R30,R31); particular preference is given to halogen;
Z is oxygen or sulfur;
X and Y are oxygen or sulfur;
A is a chemical bond, methylene, ethylene or vinylene;
R6 and R29 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C3-C6-cycloalkyl which may in turn carry one or two C1-C3-alkyl radicals, C3-C6-alkenyl, C3-C6-haloalkenyl, cyano-C1-C4-alkyl, C3-C6-alkynyl, C1-C2-alkoxy-C1-C2-alkyl, carboxyl-C1-C6-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, cyclopropylmethyl, C1-C4-alkyl which is substituted by xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-haloalkyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C3-C6-alkenyl), xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C3-C6-haloalkenyl) or xe2x80x94C(R19)xe2x95x90Nxe2x80x94Oxe2x80x94(C1-C4-alkyl)phenyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl or phenoxy-C1-C4-alkyl, the phenyl ring being able in each case to be unsubstituted or in turn to carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl and C2-C6-alkenyl, 5- or 6-membered heteroaryl or heteroaryl-C1-C6-alkyl, the heteroaromatic radical containing in each case from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able if desired to carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-alkyl;
R7,R8,R13,R30,R31, R32 and R33 independently of one another are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, cyano-C1-C4-alkyl, carboxyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, (C3-C6-cycloalkoxy)carbonyl-C1-C4-alkyl, tetrahydrofuran-2-on-3-yl, phenyl, phenyl-C1-C4-alkyl, the phenyl ring being able in each case to be unsubstituted or to carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, 5- or 6-membered heteroaryl or heteroaryl-C1-C4-alkyl, the heteroaromatic radical containing from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, and the heteroaromatic radical being able if desired to carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl; or
R7 and R8 and/or R30 and R31 together are a tetramethylene, pentamethylene or ethyleneoxyethylene chain which may if desired carry from one to three C1-C4-alkyl radicals and/or a radical xe2x80x94COOR6;
R9 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C7-cycloalkyl which may in turn carry from one to three radicals selected from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy, phenyl or phenyl-C1-C6-alkyl in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl;
R10 is hydrogen, C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl or the equivalent of an agriculturally usable cation;
R11 and R12 independently of one another are C1-C4-alkyl, C1-C4-haloalkyl, phenyl or thienyl, the phenyl or thienyl ring being able to be unsubstituted or to carry from one to three radicals selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio and C1-C4-haloalkyl, or 5- or 6-membered heteroaryl containing from one to three heteroatoms selected from the group consisting of 2 nitrogen atoms and one oxygen atom, the heteroaromatic radical being able to be unsubstituted or if desired to carry on each substitutable ring member a substituent in each case selected from the group consisting of hydroxyl, halogen, C1-C4-alkyl and C1-C4-alkoxy;
R16 is hydrogen or C1-C4-alkyl;
R17 is C1-C4-alkyl, C3-C6-cycloalkyl or phenyl;
R18 is hydrogen or C1-C4-alkyl;
R19 is hydrogen or C1-C4-alkyl;
R20 is hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl or di-(C1-C4-alkoxy)-C1-C4-alkyl;
R21 and R22 independently of one another are C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy-C1-C4-alkyl;
R23,R24,R25,R26,R27,R28 independently of one another are hydrogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or xe2x80x94COxe2x80x94Oxe2x80x94R20.
The organic molecular moieties indicated for the substituents R1 to R34 or as radicals on (hetero)aromatio structures representxe2x80x94like the definition halogenxe2x80x94collective terms for individual enumerations of the specific group members. All carbon chains, that is all alkyl, alkylcarbonyl, haloalkylcarbonyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, phenylalkyl, carboxyalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylsulfonyl moieties and the xcex1-alkylalkylidene moiety, may be straight-chain or branched. Halogenated substituents preferably carry from one to five identical or different halogen atoms.
Specific examples are:
for halogen: fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine;
for C1-C6-alkyl and the C1-C6-alkyl moieties of carboxy-C1-C6-alkyl, (C1-C8-alkoxy)carbonyl-C1-C6-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy)carbonyl-C1-C6-alkyl, (C1-C8-alkoxy)carbonyl-C1-C6-alkyl, C3-C9-(xcex1-alkylalkylidene)iminooxy-C1-C6-alkyl, phenyl-C1-C6-alkyl, phenoxy-C1-C6-alkyl, heteroaryl-C1-C6-alkyl, phenyl-C1-C6-alkyl and heteroaryloxy-C1-C6-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably C1-C4-alkyl, especially methyl and ethyl;
for C1-C8-alkyl and the alkyl moiety of cyano-C1-C8-alkyl: C1-C6-alkyl as mentioned above and, for example, n-heptyl and n-octyl, preferably C1-C6-alkyl, especially methyl and ethyl;
for C1-C4-alkyl and the alkyl moieties of C1-C6-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, di-(C1-C4-alkoxy)-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, (C1-C6-alkoxy)carbonyl-C1-C4-alkyl, di-[(C1-C6-alkoxy)carbonyl]-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, (C3-C6-cycloalkoxy) carbonyl-C1-C4-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy)carbonyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, (1,3-dioxolan-2-yl)-C1-C4-alkyl, (1,3-dioxan-2-yl)-C1-C4-alkyl and heteroaryl-C1-C4-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, preferably methyl and ethyl;
for C1-C3-alkyl radicals: methyl, ethyl, n-propyl and 1-methylethyl, preferably methyl;
for C2-C8-alkenyl: C2-C6-alkenyl such as ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yL, 1-methyl-but-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methyl-but-1-en-1-yl, 1-methyl-but-2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-1-en-2-yl, 1-ethyl-prop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-1-yl, 4-methyl-pent-2-en-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl-pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1,2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-1-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl-prop-2-en-1-yl, and, for example, for n-hept-2-en-1-yl, hept-3-en-1-yl, n-oct-2-en-1-yl and oct-3-en-1-yl, preferably C2-C6-alkenyl;
for C3-C6-alkenyl and the alkenyl moiety of heteroary-C3-C6-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methyl-but-1-en-1-yl, 1-methyl-but-2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-1-en-2-yl, 1-ethyl-prop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-1-yl 4-methyl-pent-2-en-1-yl, 3-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl-pent-3-en-1-yl, 3-methyl-pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1,2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethyl-prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl-prop-2-en-1-yl, preferably C3- or C4-alkenyl;
for C2-C8-alkynyl, for example: ethynyl, prop-1-yn-1-yl, prop-2-yn-3-yl, n-but-1-yn-1-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-1-yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl and 4-methyl-pent-2-yn-5-yl, preferably C2-C6-alkynyl, especially ethynyl and prop-2-yn-3-yl;
for C3-C6-alkynyl and the alkynyl moiety of heteroaryl-C3-C6-alkynyl: prop-1-yn-1-yl, prop-2-yn-3-yl, n-but-1-yn-1yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-1yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl and 4-methyl-pent-2-yn-5-yl, preferably C3- or C4-alkynyl, especially ethynyl and prop-2-yn-3-yl;
for C1-C8-haloalkyl: C1-C8-alkyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloropropyl and heptafluoropropyl, preferably C1-C6-haloalkyl;
for C1-C6-haloalkyl: C1-C6-alkyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloropropyl and heptafluoropropyl, preferably C1-C4-haloalkyl, especially trifluoromethyl and 1,2-dichloroethyl;
for C1-C4-haloalkyl: C1-C4-alkyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 3-chloropropyl and heptafluoropropyl, preferably trifluoromethyl and 1,2-dichloroethyl;
for C2-C8-haloalkenyl; C2-C8-alkenyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. 2-chloroallyl, 3-chloroallyl and 3,3-dichloroallyl, preferably C2-C6-haloalkenyl;
for C3-C6-haloalkenyl: C3-C6-alkenyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. 2-chloroallyl, 3-chloroallyl and 3,3-dichloroallyl;
for C2-C8-haloalkynyl: C2-C8-alkynyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, preferably C2-C6-haloalkynyl;
for cyano-C1-C4-alkyl: cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyano-but-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl and 2-cyanomethyl-prop-2-yl, preferably 2-cyanoeth-1-yl;
for cyano-C1-C8-alkyl: cyano-C1-C4-alkyl as mentioned above, preferably 2-cyanceth-1-yl;
for phenyl-C1-C4-alkyl: benzyl, 1-phenyleth-1-yl, 2-phenyleth-1-yl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenyl-prop-1-yl, 1-phenylprop-2-yl, 2-phenylprop-2-yl, 1-phenyl-but-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenyl-but-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 1-phenyl-but-3-yl, 2-phenylbut-3-yl, 1-phenyl-2-methyl-prop-3-yl, 2-phenyl-2-methyl-prop-3-yl, 3-phenyl-2-methyl-prop-3-yl and 2-benzyl-prop-2-yl;
for oarboxy-C1-C4-alkyl: carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, 1-carboxyprop-1-yl, 2-carboxyprop-1-yl, 3-carboxyprop-1-yl, 1-carboxybut-1-yl, 2-carboxybut-1-yl, 3-carboxybut-1-yl, 4-carboxybut-1-yl, 1-carboxybut-2-yl, 2-carboxybut-2-yl, 3-carboxybut-2-yl, 3-carboxybut-2-yl, 4-carboxybut-2-yl, 1-(carboxymethyl)eth-1-yl, 1-(carboxymethyl)-1-(methyl)-eth-1-yl and 1-(carboxymethyl)-prop-1-yl, preferably carboxymethyl and 2-carboxyethyl;
for carboxy-C1-C6-alkyl: carboxy-C1-C4-alkyl as mentioned above, and 5-carboxypent-1-yl, preferably carboxy-C1-C4-alkyl;
for C1-C4-alkoxy and the alkoxy moieties of C1-C4-alkoxy-C1-C4-alkyl, di-(C1-C4-alkoxy)-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy) carbonyl-C1-C6-alkyl, C1-C4-alkoxy-(C1-C4-alkoxy) carbonyl-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methyl-propoxy, 2-methylpropoxy and 1,1-dimethylethoxy, preferably methoxy, ethoxy and 1-methylethoxy;
for C1-C6-alkoxy and the alkoxy moiety C1-C6-alkoxy-C1-C4-alkyl C1-C4-alkoxy as mentioned above, and n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, preferably methoxy, ethoxy and 1-methylethoxy;
for C1-C8-alkoxy: C1-C6-alkoxy as mentioned above and, for example, n-heptoxy and n-octoxy, preferably C1-C6-alkoxy, especially methoxy, ethoxy and 1-methylethoxy;
for C1-C4-alkylthio and the alkylthio moiety of C1-C4-alkylthio-C1-C4-alkyl: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio, preferably methylthio, 5 ethylthio and 1-methylethylthio;
for C1-C6-alkylthio: C1-C4-alkylthio as mentioned above and n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, preferably methylthio, ethylthio and1-methylethylthio;
for (C1-C4-alkyl)carbonyl: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1,1-dimethylethylcarbonyl, preferably methylcarbonyl, ethylcarbonyl and n-propylcarbonyl;
for (C1-C4-haloalkyl)carbonyl: C1-C4-alkylcarbonyl as mentioned above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, fluoromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chlorofluoromethylcarbonyl, dichlorofluoronethylcarbonyl, chlorodifluoromethylcarbonyl, 1-fluoroethylcarbonyl, 2-fluoroethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoro- ethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 3-chloropropylcarbonyl and heptafluoropropylcarbonyl, preferably trifluoromethylcarbonyl and 1,2-dichloroethylcarbonyl;
for (C1-C6-alkoxy)carbonyl and the alkoxycarbonyl moieties of (C1-C6-alkoxy)carbonyl-C1-C4-alkyl and di-[(C1-C6-alkoxy)-carbonyl]-C1-C4-alkyl: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbony, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl and 1-ethyl-2-methyl-propoxycarbonyl, preferably (C1-C4-alkoxy)carbonyl, especially methoxycarbonyl, ethoxycarbonyl and 1-methylethoxycarbonyl;
for the alkoxycarbonyl moiety of (C1-C8-alkoxy) carbonyl-C1-C6-alkyl: (C1-C6-alkoxy)carbonyl as mentioned above and, for example, n-heptoxycarbonyl and n-octoxycarbonyl, preferably (C1-C6-alkoxy)carbonyl, especially methoxycarbonyl, ethoxycarbonyl and 1-methylethoxycarbonyl;
for the alkylsulfonyl moiety of C1-C4-alkylsulfonyl-C1-C4-alkyl: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl, preferably methylsulfonyl and ethylsulfonyl;
for the C3-C9-(xcex1-alkylalkylidene) moiety of C3-C9-(xcex1-alkylalkylidene)iminooxy-C1-C6-alkyl, for example: xcex1-methylethylidene, xcex1-methylpropylidene and xcex1-ethylpropylidene, especially xcex1-methylethylidene;
for C3-C6-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, preferably cyclopropyl and cyclopentyl;
for C3-C7-cycloalkyl: C3-C6-cycloalkyl as mentioned above and cycloheptyl, preferably cyclopropyl and cyclopentyl;
for C3-C8-cycloalkyl: C3-C6-Cycloalkyl as mentioned above and cycloheptyl and cyclooctyl, preferably cyclopropyl, cyclopentyl and cyclohexyl;
for C5-C7-cycloalkenyl: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2-enyl, cyclohept-3-enyl and cyclohept-4-enyl, preferably cyclopent-1-enyl;
for the cycloalkoxycarbonyl moiety of (C3-C6-cycloalkoxy) carbonyl-C1-C4-alkyl; cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentoxycarbonyl and cyclohexoxycarbonyl, preferably cyclopropoxycarbonyl and cyclopentoxycarbonyl;
5- or 6-membered heteroaryl and the heteroaryl moiety of heteroaryl-C1-C4-alkyl: for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, preferably 3-pyrazolyl, 2-pyridyl and 2-thienyl.
Particularly suitable agriculturally usable cations are those cations which do not have an adverse effect on the herbicidal activity of the compounds I, especially the ions of alkali metals, preferably sodium and potassium, of alkaline earth metals, preferably calcium, magnesium and barium, and of transition metals, preferably manganese, copper, zinc and iroh, and the ammonium ion, which may if desired carry from one to three C1-C4-alkyl or hydroxy-C1-C4-alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl-(2-hydroxyethyl)-ammonium, and also phosphonium ions, sulfonium ions, preferably tri-(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri-(C1-C4-alkyl)sulfoxonium.
The 3-phenylpyrazole derivatives of the formula I can be obtained in a number of ways, preferably by one of the following processes:
A) Reaction of a xcex2-ketocarboxylic acid derivative III with hydrazine or a hydrazine derivate in an inert solvent (cf. eg. JP-A 04/225 937 and JP-A 03/072 460) and alkylation of the product IV: 
is a suitable leaving group such as halogen, xe2x80x94Oxe2x80x94SO2CH3, xe2x80x94Oxe2x80x94SO2CF3, xe2x80x94Oxe2x80x94SO2C4F9 or xe2x80x94Oxe2x80x94SO2(pxe2x80x94CH3-C6H4);
R35 is preferably C1-C4-alkoxy, C1-C4-alkylcarbonyloxy or halogen
The solvent may be aprotic or protic. Examples of suitable solvents are organic acids such as acetic acid, hydrocarbons, halogenated hydrocarbons, ethers such as ethylene glycol dimethyl ether, alcohols such as methanol and ethanol, and sulfoxides.
The reaction temperature is determined primarily by the melting point of the compound III and the boiling point of the reaction mixture. It is preferably from about 60 to 120xc2x0 C.
Generally from 0.95 to 5 times the molar quantity, advantageously from 1 to 1.4 times the quantity, of hydrazine or hydrazine derivative is employed, based on the xcex2-ketocarboxylic acid derivative III.
The quantity of alkylating agent L-R4 is commonly likewise from 095 to 5 times the molar quantity, based on the intermediate IV.
In view of the preferred radicals R3 on the 3-phenylpyrazoles I, particular preference is given to those hydrazine derivatives which carry an alkyl group.
Alkylation is normally carried out with the halide, preferably the chloride or bromide, or with the sulfate of an alkane or haloalkane, if desired in the presence of an organic base, for example a trialkylamine or pyridine, or an inorganic base, for example an alkali metal carbonate.
The alkylation is advantageously carried out in an inert organic solvent, for example in an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane, in an aliphatic ketone such as acetone, in an amide such as dimethylformamide, in a sulfoxide such as dimethyl sulfoxide, or in a mixture of one of these solvents and water.
The reaction can generally be carried out at from 0xc2x0 C. to the boiling temperature of the reaction mixture. It is preferably carried out from about 20 to 80xc2x0 C.
When Z=S the product can be oxidized to the sulfoxide or sulfone in a manner known per se (cf. eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 9, Georg Thieme Verlag, Stuttgart, 4th Edition 1955, p. 211ff and 227ff; Org. Synth. Coll. Vol. V, 791): 
B) Halogenation of compounds I where R5=hydrogen: 
The reaction can be carried out in an inert solvent or diluent or without solvent.
Examples of suitable solvents are organic acids, inorganic acids, hydrocarbons, halogenated hydrocarbons, aromatic hydrocarbons, ethers, sulfides, sulfoxides and sulfones.
Examples of suitable halogenating agents are chlorine, bromine, N-bromosuccinimide, N-chlorosuccinimide or sulfuryl chloride. Depending on the starting compounds and halogenating agent, the addition of a free-radical initiator, for example an organic peroxide such as dibenzoyl peroxide or an azo compound such as azobisisobutyronitrile, or irradiation with light, may have an advantageous effect on the course of the reaction.
The quantity of halogenating agent is not critical. Both substoichiometric amounts and large excesses of halogenating agent, based on the compound I where R5=hydrogen which is to be halogenated, are possible.
If a free-radical initiator is used it is generally adequate to employ a catalytic amount.
The reaction temperature is normally from xe2x88x92100 to 200xc2x0 C., ideally at from 10 to 100xc2x0 C., or at the boiling point of the reaction mixture.
C) Nitration of compounds I where R1=hydrogen: 
Examples of suitable nitrating reagents are nitric acid in various concentrations, including concentrated and fuming nitric acid, mixtures of sulfuric acid and nitric acid, acetyl nitrates and alkyl nitrates.
The reaction can either be carried out without solvent in an excess of the nitrating reagent or in an inert solvent or diluent, suitable examples being water, inorganic acids, organic acids, chlorinated hydrocarbons such as methylene chloride, anhydrides such as acetic anhydride, and mixtures of these solvents.
The starting compound I where R1=H and the nitrating reagent are advantageously employed in approximately equimolar quantities; in order to optimize the conversion of the compound to be nitrated, however, it may be advantageous to use the nitrating reagent in excess, up to about 10 times the molar quantity. When the reaction is carried out without solvent in the nitrating reagent, the latter is present in an even greater excess.
The reaction temperature is normally from xe2x88x92100 to 200xc2x0 C., preferably from xe2x88x9230 to 50xc2x0 C.
The reaction mixture can be worked up in a known manner, for example by diluting the reaction solution with water and then isolating the product by filtration, crystallization or solvent extraction.
D) Reduction of compounds I where R1=nitro: 
D1) Reduction with a metal such as iron, zinc or tin under acid reaction conditions or by means of complex hydrides such as lithium alumlinium hydride and sodium borohydride:
The solvent, for example water, an alcohol such as methanol, ethanol or isopropanol or an ether such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether, is dependent on the chosen reducing agent.
Reduction with a metal is preferably carried out without solvent in an inorganic acid, especially concentrated or dilute hydrochloric acid, or in an organic acid such as acetic acid. However, it is also possible to mix in with the acid an inert solvent as mentioned above.
The starting compound I (R1=NO2) and the reducing agent are advantageously employed in approximately equimolar quantities; in order to optimize the course of the reaction, however, it may be advantageous to use one of the two components in excess, up to about 10 times the molar quantity.
The quantity of acid is not critical. In order to maximize reduction of the starting compound it is advantageous to use at least an equivalent quantity of acid.
The reaction temperature is generally fromxe2x88x9230 to 200xc2x0 C., preferably 0 to 80xc2x0 C.
After the end of the reaction the reaction mixture is normally diluted with water and the product is isolated by filtration, crystallization or extraction with a solvent which is substantially immiscible with water, for example with ethyl acetate, diethyl ether or methylene chloride. If desired, the product can subsequently be purified in the known manner.
D2) Catalytic hydrogenation with hydrogen:
Examples of suitable catalysts are Raney nickel, palladium on charcoal, palladium oxide, platinum and platinum oxide, a sufficient quantity of catalyst generally being from 0.05 to 10.0 mol %, based on the compound to be reduced.
The reaction is carried out either without solvent or in an inert solvent or diluent, for example in acetic acid, a mixture of acetic acid and water, ethyl acetate, ethanol or toluene.
After the catalyst has been separated off the reaction solution can be worked up to the product in a conventional manner.
Hydrogenation can be carried out at atmospheric pressure or superatmospheric pressure.
E) Compounds I in which R1 is xe2x80x94N(R7,R8) and R7 and R8 are hydrogen can, for example, be alkylated, acylated, sulfonylated, hydroxylated or diazotized in a known manner (in this respect see Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Volume E16d, part 2, Georg Thieme Verlag, Stuttgart, 4th Edition 1992, pages 1241 to 1314 and the literature cited therein): 
Further reactions are possible subsequently, for example Sandmeyer reactions {cf. eg. H. H. Hodgson, Chem. Rev. 40, (1947) 251 and Houben-Weyl, Methoden der Organischen Chemie [Methods of organic Chemistry], Vol. 5/4, Georg Thieme Verlag, Stuttgart, 4th Edition 1960, p. 438}, Meerwein reactions {see eg. M. Doyle, B. Siegfried. R. C. Elliot, J. F. Dellaria, J. Org. Chem. 42, (1977) 2431}, boiling with phenol (see eg. Org. Synth. Coll. Vol. 3, (1955) 130} or the reduction of the diazonium salt of I (R1=NH2) to the corresponding arylhydrazine (see eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. E16a, Georg Thieme Verlag, Stuttgart, 4th Edition 1990, p. 656ff.). The arylhydrazines may in turn be acylated in a conventional manner (cf. in this respect eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. E16a, Georg Thieme Verlag, Stuttgart, 4th Edition 1990, p. 828ff.).
The acylhydrazines obtained in this way can in turn be oxidized to azo compounds (see eg. Houben-Weyl, Methoden der Organischen Chemie, Vol. E16d, Georg Thieme Verlag, Stuttgart, 4th Edition 1992, p. 102f.).
F) Halogenation of compounds I in which R1 is methyl: 
Hal =halogen, preferably chlorine or bromine.
With regard to solvents, proportions and the reaction temperature, reference is made to the comments under method B).
G) Nucleophilic substitution of a halogen atom in compounds I where R1=CH2Hal: 
Examples of suitable nucleophiles are alkoxides, thioalkoxides, aryl or alkyl anions, amines, cyanides, alcohols, thiols or salts of carboxylic acids or trialkyl phosphites; use of the latter gives rise to phosphonates (R1=xe2x80x94CH2xe2x80x94P(O)(OR6)2; Arbuzov reaction; see eg. A. R. Katritzky, B. Pilarski, Org. Prep. Proced. Int. 22 (1990) 209).
Depending on the starting compound and nucleophile, it may be advantageous to add a base, for example an organic base such as a trialkylamine or diazobicycloundecene or an inorganic base such as potassium carbonate or sodium carbonate or an alkali metal hydroxide.
The quantity of base is preferably from 0.95 to 10 mol, in particular from about 1 to 3 mol, per mole of starting compound.
Particularly preferred solvents are dimethylformamide, dimethylacetamide, acetone, dimethyl sulfoxide, dioxane, water and a mixture of these solvents.
A further possibility is to carry out the reaction in a 2-phase system comprising water and an organic solvent which is substantially immiscible with water, for example methylene chloride. In this variant, in order to improve the course of the reaction it is advantageous to add a phase transfer catalyst, for example an ammonium salt such as benzyltrialkylammonium halide and tetrabutylammonium halide (with regard to phase transfer catalysis, see also Synthesis 1976, 113).
It is generally adequate to employ a catalytic quantity of phase transfer catalyst, for instance between 1 and 10 mol % based on the starting compound.
The reaction temperature depends on the choice of nucleophile. When aryl or alkyl anions are used, this temperature is from about xe2x88x92150 to 0xc2x0 C., preferably from xe2x88x9278 to xe2x88x9220xc2x0C. For the other nucleophiles mentioned above, it is usually necessary to employ a higher reaction temperature, for instance from 0 to 100xc2x0 C.
Those end products I in which R1 is xe2x88x92CH2xe2x80x94OR6 where R6=(C1-C4-alkyl) carbonyl, can be hydrolyzed subsequently in a manner known per se to give compounds I where R1=xe2x80x94CH2OH. The hydrolyzed products can then if desired be alkylated, acylated or sulfonated, to give further compounds within the definition for I where R1=xe2x80x94CH2OR6 (R6xe2x89xa0H) (see eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg Thieme Verlag, Stuttgart: Vol. 6/1a , 4th Edition 1979, p. 262ff.; Vol. 8, 4th Edition 1952; p. 516ff.; Vol. 6/3, 4th Edition 1965, p. 10off.; Vol. 9, 4th Edition 1955, p. 343ff. and 659ff.).
H) Acid hydrolysis of compounds I in which R1 is dihalomethyl: 
The hydrolysis is preferably carried out without solvent in an acid such as hydrochloric acid, sulfuric acid or acetic acid, specially concentrated sulfuric acid, or in a mixture of acetic acid and water (eg. 3:1).
The reaction temperature is usually from 0 to 120xc2x0 C.
The reaction product can generally be worked up in a manner known per se.
I) Oxidation of compounds I in which R1 is halomethyl in a manner known per se, eg. according to Kornblum (in this respect see in particular pages 179 to 181 of xe2x80x9cMethods for the Oxidation of Organic Compoundsxe2x80x9d by Alan H. Haines, Academic Press 1988, in the series xe2x80x9cBest Synthetic Methodsxe2x80x9d): 
Dimethyl sulfoxide is one example of a suitable solvent.
K) Oxidation of compounds I in which R1 is formyl: 
Examples of suitable inert solvents are water, hydrocarbons, aromatic hydrocarbons or pyridine and derivatives thereof.
Examples of suitable oxidizing agents are potassium permanganate, potassium dichromate, sodium perborate, sodium chlorite, hydrogen peroxide and oxygen.
The reaction temperature depends in particular on the reaction medium. It is preferably from 0 to 120xc2x0 C.
Working up to give the product is carried out in the conventional manner.
The further reaction of the product to give the corresponding acid derivatives or ketone derivatives may take place in a manner known per se (see in this respect in particular parts 1 and 2 of Volume E5 of Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry]).
L) Halosulfonation of compounds I in which R1 is xe2x80x94SO2-Cl: 
The halosulfonation can be carried out without solvent in an excess of sulfonating reagent or in an inert solvent, for example in a halogenated hydrocarbon, an ether, an alkanenitrile or a mineral acid.
Chlorosulfonic acid is both the preferred reagent and solvent.
The sulfonating reagent is normally employed in a slightly substoichiometric quantity (up to about 95 mol %) or in an excess of from 1 to 5 times the molar quantity, based on the starting compound I (R1=H). If the reaction is carried out without inert solvent then an even greater excess may be advantageous.
The reaction temperature is normally between 0xc2x0 C. and the boiling point of the reaction mixture.
For working up the product, water for example is added to the reaction mixture, after which the product can be isolated in a conventional manner.
M) Reaction of compounds I in which R1 is xe2x80x94SO2-Cl with carbon, oxygen or nitrogen nucleophiles to give the corresponding sulfonic acids, sulfonates or sulfonamide derivates in a manner known per se (see in this respect in particular page 351 of xe2x80x9cThe Chemistry of Sulphonic Acids, Esters and their Derivativesxe2x80x9d, John Wiley and Sons 1991, in the series xe2x80x9cThe Chemistry of Functional Groupsxe2x80x9d and p. 530f. in Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 9, Georg Thieme Verlag, Stuttgart, 4th Edition 1955): 
N) Reduction of compounds I in which R1 is xe2x80x94SO2-C1 to give the corresponding thiols in a manner known per se (see in this respect, in particular, page 216 of xe2x80x9cThe Chemistry of the Thiol Groupxe2x80x9d, John Wiley and Sons 1974, in the series xe2x80x9cThe Chemistry of Functional Groupsxe2x80x9d): 
Examples of suitable reducing agents are transition metals such as iron, zinc and tin.
The compounds I in which R1 is the thiol group can be converted in a manner known per se (cf. eg. p. 721 of xe2x80x9cThe Chemistry of Sulphonic Acids, Esters and their Derivativesxe2x80x9d, John Wiley and Sons 1991, in the series xe2x80x9cThe Chemistry of Functional Groupsxe2x80x9d) to compounds of the formula I in which R1 is xe2x80x94SR6 (R6 xe2x89xa0hydrogen). The group xe2x80x94SR6 may in turn be oxidized in a manner known per se {in this context see the details under method A)} to xe2x80x94SOxe2x80x94R6 and xe2x80x94SO2xe2x80x94R .
O) Conversion of compounds I in which R1 is formyl, in a manner known per se, to the corresponding oximes (see eg. HoubenWeyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 10/4, Georg Thieme Verlag, Stuttgart, 4th Edition 1968, p. 55ff. and p. 73ff.), acetals (see in this respect eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 6/3, Georg Thieme verlag, Stuttgart, 4th Edition 1965, p. 221ff. and p. 250ff.) or alkenes (cf. eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 5/16, Georg Thieme Verlag, Stuttgart, 4th Edition 1972, p. 383ff.): 
P) Nucleophilic cyanide substitution of compounds I where R1=
M is a metallic or orgnaic cation, preferably an alkali metal or tetraalkylammonium ion.
The reaction is normally carried out in a polar aprotic solvent such as dimethyl sulfoxide, N,N-dimethylformamide and sulfolane, the reaction temperature lying between its melting and boiling points, in particular at from 0 to 100xc2x0 C.
It is preferred to employ a slight molar excess of the cyanide MCN. In order to optimize the conversion, however, it may be advantageous to use a large excess of MCN, for instance up to five times the molar quantity, based on the quantity of starting compound I where R2=fluorine.
The reaction mixture can be worked up in a manner known per se, for example by diluting the reaction mixture with water and then isolating the product by filtration, crystallization or solvent extraction.
Q) Nucleophilic alcoholate substitution of compounds I where R1=NO2 and R2=CN in a manner known per se (see eg. Houbenweyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 6/3, Georg Thieme Verlag, Stuttgart, 4th Edition 1965, p. 75ff.); compounds I where R1=OR6,R2=CN and R6=lower alkyl can preferably be prepared in this manner: 
The product I (R1=OR6,R2=CN) may if desired be cleaved in a manner known per se to give compounds I where R1=OH (R2=CN) (cf. eg. Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Vol. 6/1c, Georg Thieme Verlag Stuttgart, 4th Edition 1976, p. 313ff.).
Compounds I where R1=hydroxyl, which are accessible in this manner or by means of the phenol boiling method described under E), may if desired be alkylated, acylated or sulfonated in a manner known per se, as described under G) for compounds I where R1=xe2x80x94CH2OH.
Unless otherwise indicated, the reactions described above are advantageously carried out at atmospheric pressure or under the autogenous pressure of the particular reaction mixture.
The preparation of the substituted 3-phenylpyrazoles I may produce isomer mixtures which, however, may if desired be separated into the pure isomers by the methods which are conventional for this purpose, such as crystallization or chromatography, possibly on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting compounds.
Substituted 3-phenylpyrazoles I in which R10 is an alkali metal can be obtained by treating compounds I where R10=hydrogen, for example
with sodium hydroxide or potassium hydroxide in aqueous solution or in an organic solvent such as methanol, ethanol, acetone or toluene, or
with sodium hydride in an organic solvent such as dimethylformamide.
Substituted 3-phenylpyrazoles I in which R10 is an agriculturally usable cation other than an alkali metal may be prepared conventionally by salt exchange of the corresponding compound I where R10=an alkali metal ion.
Compounds I in which R10 is, for example, manganese, copper, zinc, iron, calcium, magnesium or barium ion may be prepared in a conventional manner from compounds I where R10=sodium, and from compounds I where R10=ammonium or phosphonium ion, using ammonia, phosphonium hydroxides, sulfonium hydroxides or sulfoxonium hydroxides.
Using the process described it is also possible to obtain all other salts of agriculturally usable cations of the compounds I, for example those derived from compounds I (R1=xe2x80x94SO2xe2x80x94OR6; R6=H), (R1=xe2x80x94SO2xe2x80x94N(R7)xe2x80x94COxe2x80x94R9; R7=H), (R1=xe2x80x94N(R10)xe2x80x94SO2xe2x80x94R10; R10=H), (R1=xe2x80x94Axe2x80x94COxe2x80x94NHxe2x80x94SO2xe2x80x94(C1-C4-alkyl)) or (R1=xe2x80x94Axe2x80x94P(O)(OR6)2,R6=H).
Those compounds I which carry a basic functional group, for example if R1 is xe2x80x94N(R7,R8), xe2x80x94N(R7)xe2x80x94N(R8,R32), xe2x80x94Nxe2x95x90Nxe2x80x94COR9 or xe2x80x94N(R7)xe2x80x94N(R8)xe2x80x94COxe2x80x94R9, and those compounds I containing the functional group  greater than Cxe2x95x90Nxe2x80x94, can be converted into their acid addition salts by reaction with the corresponding acid.
The acid addition can be carried out in aqueous solution or in an organic solvent such as methanol, ethanol, acetone, toluene or ether. The acid addition salts of I may also be subjected to salt exchange, making it possible to obtain agriculturally usable salts with other anions.
The salt formation reactions normally proceed at a sufficient rate even at about 20xc2x0 C.
The salts can be isolated by, for example, precipitation with an appropriate inert solvent or by evaporating off the solvent.
The substituted 3-phenylpyrazoles I and salts thereof are suitable, both as isomer mixtures and in the form of the pure isomers, as herbicides. They are able to give very good control of broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soybean and cotton without noticeably damaging the crop plants. This effect occurs especially at low application rates.
Depending on the particular application method, the compounds I or herbicidal compositions containing them can also be employed in a further range of crop plants for the elimination of unwanted plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris ssp. altissima, Beta vulgaris ssp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Belianthus annuus, Bevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis,Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. 
Moreover, the compounds I can also be employed in crops which are substantially resistant to the action of I as a result of breeding and/or genetic manipulation methods.
The compounds I or the herbicidal compositions containing them can be applied, for example, by spraying, atomizing, dusting, scattering or watering in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting compositions, scattering compositions or granules. The application forms depend on the intended uses; if possible they should in each case guarantee the finest distribution of the active compounds according to the invention.
Suitable inert auxiliaries for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are essentially: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, coal-tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water, as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, adhesive, dispersant or emulsifier and possibly solvents or oil, which are suitable for dilution with water, can also be prepared.
Suitable surface-active substances are the alkali metal, alkaline earth metal or ammonium salts of aromatic sulfonic acids, eg. lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfate waste liquors or methylcellulose.
Powder, scattering and dusting compositions can be prepared by mixing or conjoint grinding of the active substances with a solid carrier.
Granules, eg. coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such assilicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and plant products such as cereal flour, treebark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
The concentrations of the active compounds I in the ready-to-use formulations may be varied within a wide range, for instance between 0.01 and 95% by weight, preferably between 0.5 and 90% by weight. In this context the active compounds are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
The formulation examples below illustrate the preparation of such formulations:
I. 20 parts by weight of compound No. Ia.071 are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of from 8 to 10 mol of ethylene oxide with 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring out the solution and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.
II. 20 parts by weight of compound No. Ia.047 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.
III. 20 parts by weight of the active compound No. Ia.066 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of from 210 to 2800xc2x0 C. and 10 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.
IV. 20 parts by weight of the active compound No. Ia.122 are thoroughly mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-xcex1-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of silica gel in powder form, and the mixture is ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray mixture is obtained which contains 0.1% by weight of the active compound.
V. 3 parts by weight of the active compound No. Ia.161 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dusting composition is obtained which contains 3% by weight of the active compound.
VI. 20 parts by weight of the active compound No. Ia.171 are intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
The application of the active compounds I or of the herbicidal composition can be carried out pre-emergence or post-emergence. If the active compounds are less tolerable for certain crop plants, then application techniques can be employed in which the herbicidal compositions are sprayed with the aid of spray equipment such that the leaves of the sensitive crop plants are if possible not affected, while the active compounds reach the leaves of unwanted plants growing under them or the uncovered soil surface (post-directed, lay-by).
Depending on the aim of control, time of year, target plants and growth stage, the application rates of active compound are from 0.001 to 3.0, preferably from 0.1 to 1, kg/ha of active substance (a.s.).
To widen the spectrum of action and to achieve synergistic effects, the substituted 3-phenylpyrazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied jointly. For example, suitable co-components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylic acids, tria Z ines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives which carry eg. a carboxyl or carbimino group in position 2, quinolinecarboxylic derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy- and heteroaryloxyphenoxypropionic acids and their salts, esters and amides and others.
Additionally, it may be useful to apply the compounds I on their own or together in combination with other herbicides, additionally mixed with further plant protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the possibility of mixing with mineral salt solutions, which are employed for the elimination of nutritional and trace element deficiencies. Nonphytotoxic oils and oil concentrates can also be added.